Located just off of the main drag of Damen Avenue in Bucktown, Urban Holiday Lofts is tucked away in a cozy pocket just steps from the hustle and bustle of the swanky and ever-evolving neighborhood. Stock up on local gourmet snacks from Olivia’s Market, located on our ground level, and set your sights on exploring the hood. Meander in and out of the shops on Damen like P.45, Scotch & Soda, RSVP Gallery, Diptyque, Robin Richman, Shinola, and Nike Running Bucktown or indulge in Bucktown’s thriving restaurant scene at spots like Le Bouchon, Hot Chocolate, Presidio, and the notorious honky tonk taco joint, Big Star. Satisfy your sweet tooth with a stop at the venerable Margie’s Candies with an iconic ice cream sundae, and then walk it off on The 606 to get a view of the neighborhood from new heights. For those looking to imbibe, Bucktown and neighboring Wicker Park play home to some of Chicago’s most talked about bars such as Danny’s Liquors, award-winning Violet Hour, Revel Room, and The Map Room (Perhaps the best selection of brews in the city and brimming with travel inspiration!).

Once you’ve tackled the neighborhood, head downtown to check out some of the city’s iconic landmarks and top attractions. Just steps away from Urban Holiday Lofts, hop on the Blue Line at the Damen stop for a short ride to the heart of the city. Wander the halls of the Art Institute, snap a selfie at the Bean, catch sprawling city views atop the Willis Tower, and take in the world-famous skyline on the Architectural Cruise tour. Rent a Divvy bike at the Navy Pier and ride north towards Lincoln Park along the lake, taking in picturesque views of the cityscape and Chicago’s many harbors. After all that you’ll have worked up quite the appetite, so dig your teeth into Chicago’s iconic deep dish pizza at Lou Malnati’s or head to Portillo’s for a Chicago-style hot dog and see what all the fuss is about.

A city of neighborhoods, Chicago is filled with cultural flavor and has something to satisfy every traveler’s appetite. Navigate the city with ease and grab a city pass here

Here are some of our favorite restaurants, bars, shops, tours, and sights:


Enjoy a wide variety of sightseeing tours and cruises while you’re here. Our most popular tours are the Architectural Tours by Boat and the Chicago Trolley Tour. The city also offers exceptional Dinner Cruises, as well as dinner show tickets and bus tours. Chicago Tours features a variety of bus tours, bike tours, Segway tours, shopping and food tours, and boat tours to show you the great sights of the great city of Chicago. See the Willis Tower, enjoy a fabulous Dinner Show, Rent a Bike or enjoy a Ghost Tour.

Enjoy a seamless glide, as you experience spectacular views of Chicago’s breathtaking Lakefront, while riding on the newest technology of Segway Personal Transporters. With countless attractions, gorgeous parks and dazzling gardens your tour guides will ensure you receive the most stunning photo opportunities.

Enjoy a cruise of the historic Chicago River that showcases over 40 landmarks of modern American architecture. Join us on an exciting journey as we tour the Chicago River and its architectural landmarks.

This comprehensive trolley tour of the Windy allows you to hop on and hop off at a number of popular locations. Trolley stops include Willis Tower, Art Institute, Museum Campus, Water Tower, Wrigley Building and Fort Dearborn.